Dimethylamine → N,N-Dimethyl-1-cyclohexan-1-amine

HRID 614571Notes

Reaction equation

HRID 614571 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]1(=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>[Ti](Cl)(Cl)(Cl)Cl.CCOCC>[CH3:1][N:2]([CH3:3])[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 7967Cyclohexanone

Product 1

HCID 139609N,N-Dimethyl-1-cyclohexan-1-amine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Titanium tetrachloride (237 g., 1.25 mole) is added in small portions over 4 hrs. to a solution of dimethyl amine (307 g., 6.82 mole) and cyclohexanone (223 g., 2.27 mole) in 600 ml. ether. Temperature is maintained below 5° during the addition. The mixture is stirred overnight at room temperature. The precipitate is collected and washed with ether. The ether is removed by distillation and the residual oil distilled at reduced pressure. After a small forerun, 243 g. (86% yield) of enamine (title compound) is obtained, b.p. 79°-80° (33 mm. Hg.) The nmr (CDCl3) is in accord.

Workup

  1. temperatureTemperature is maintained below 5° during the addition
  2. customThe precipitate is collected
  3. washwashed with ether
  4. customThe ether is removed by distillation
  5. distillationthe residual oil distilled at reduced pressure

Sources & evidence

ORD record
ord-5054dfbf69d64f82bef0732202766882
Source dataset
uspto-grants-1979_03
Patent number
US04145435

Reaction notes

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